This invention relates to certain thiophene ketones, their agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
EP 283,261 discloses heterocycles of Formula i as herbicides: ##STR3## wherein X, X.sup.1 and X.sup.2 are independently O or S;
R.sup.1 is a monocyclic or fused-bicyclic heterocyclic group optionally substituted by one or more groups selected from oxo, mercapto, halo, nitro, cyano, amino, mono- or dialkylamino, amido, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkoxy, aryl, hydroxy, alkoxy, alkoxycarbonyl, alkylcarbonyl, mono- or dialkylcarbamoyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfonamido, alkylcarbonyloxy, alkylcarbonylamino or heterocyclyl; and PA1 Y is, inter alia, C.sub.2 -C.sub.4 alkylene. PA1 R.sup.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylsulfonyl, halogen, cyano or nitro; PA1 R.sup.3 is OR.sup.9, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylsulfonyl or halogen; PA1 each R.sup.4 is independently C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio or halogen; or when two R.sup.4 are attached to the same carbon atom, then said R.sup.4 pair can be taken together to form --OCH.sub.2 CH.sub.2 O--, --OCH.sub.2 CH.sub.2 CH.sub.2 O--, --SCH.sub.2 CH.sub.2 S-- or --SCH.sub.2 CH.sub.2 CH.sub.2 S--, each group optionally substituted with 1-4 CH.sub.3 ; PA1 R.sup.5 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, formyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylaminocarbonyl, C.sub.3 -C.sub.7 dialkylaminocarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl or C.sub.1 -C.sub.6 haloalkylsulfonyl; or PA1 R.sup.5 is benzoyl or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 R.sup.6 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; or R.sup.6 is phenyl or benzyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 R.sup.7 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, halogen, cyano or nitro; PA1 R.sup.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; PA1 R.sup.9 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C2-C.sub.6 alkoxyalkyl, formyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylaminocarbonyl, C.sub.3 -C.sub.7 dialkylaminocarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl or C.sub.1 -C.sub.6 haloalkylsulfonyl; or R.sup.9 is benzoyl or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 m is 1 or2; PA1 n is 0, 1 or 2; and PA1 p and q are each independently 0, 1, 2, 3 or 4; PA1 Preferred 1. Compounds of Formula I above, and agriculturally-suitable salts thereof, wherein: PA1 Preferred 2. Compounds of Preferred 1 wherein: PA1 2-[(5,6-dihydro-3,4,4-trimethyl-4H-thieno[2,3-b]thiopyran-2-yl)carbonyl]-1, 3-cyclohexanedione S,S-dioxide; PA1 (5,6-dihydro-3,4,4-trimethyl-4H-thieno[2,3-b]thiopyran-2-yl)(1-ethyl-5-hydr oxy-1H-pyrazol-4-yl)methanone S,S-dioxide; PA1 2-[(5,6-dihydro-3-methylspiro[1,3-dioxolane-2,4'-[4H]thieno[2,3-b]thiopyran ]-2-yl)carbonyl]-1,3-cyclohexanedione S,S-dioxide; and PA1 (5,6-dihydro-3-methylspiro[1,3-dioxolane-2,4'-[4H]thieno[2,3-b]thiopyran-]2 -yl)(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone S,S-dioxide.
The thiophene ketones of the present invention are not disclosed therein.